(6-Methyl-2-oxooxan-3-yl) trifluoromethanesulfonate | 172172-35-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (6-Methyl-2-oxooxan-3-yl) trifluoromethanesulfonate
• CAS: 172172-35-9
• 化学式: C₇H₉F₃O₅S
• 分子量: 262.207
• InChiKey: UMXGYSXQIBHWMA-UHFFFAOYSA-N

物化性质

• 沸点：
  324.4±42.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (6-Methyl-2-oxooxan-3-yl) trifluoromethanesulfonate 在 platinum on activated charcoal N-甲基哌啶 、 草酰氯 、 氢气 、 碳酸氢钠 、 二甲基亚砜 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 37.58h， 生成 (2S,5R,1'R/S)-1-benzyl-5-<1'-(methoxycarbonyl)-4'-oxopentyl>proline tert-butyl ester
  参考文献：
  名称：

  Enantiospecific Synthesis of (+)- and (−)-Ferruginine from l-Glutamic Acid. Synthesis of Tropanes via Intramolecular Iminium Ion Cyclization

  摘要：

  Iminium ions, generated by decarbonylation of N-benzyl-5-[1-(methoxycarbonyl)-4-oxopentyl]-prolines, prolines, undergo intramolecular cyclization to afford 2,4-disubstituted tropanes in good yields. This transformation is also shown to be a stereospecific reaction. The value of these substituted tropanes has been demonstrated by functional group manipulation, leading to the enantiospecific synthesis of (+)-ferruginine, an alkaloid isolated from Darlinga ferruginea, and its unnatural enantiomer, (-)-ferruginine.

  DOI：

  10.1021/jo9515081
• 作为产物：
  描述：

  丁位己内酯 在 咪唑 、 盐酸 、 甲醇 、 2,6-二叔丁基-4-甲基吡啶 、 二氯甲烷 、 双(三甲基硅烷基)氨基钾 、 2-(Phenylsulfonyl)-3-phenyloxaziridin 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.5h， 生成 (6-Methyl-2-oxooxan-3-yl) trifluoromethanesulfonate
  参考文献：
  名称：

  Enantiospecific Synthesis of (+)- and (−)-Ferruginine from l-Glutamic Acid. Synthesis of Tropanes via Intramolecular Iminium Ion Cyclization

  摘要：

  Iminium ions, generated by decarbonylation of N-benzyl-5-[1-(methoxycarbonyl)-4-oxopentyl]-prolines, prolines, undergo intramolecular cyclization to afford 2,4-disubstituted tropanes in good yields. This transformation is also shown to be a stereospecific reaction. The value of these substituted tropanes has been demonstrated by functional group manipulation, leading to the enantiospecific synthesis of (+)-ferruginine, an alkaloid isolated from Darlinga ferruginea, and its unnatural enantiomer, (-)-ferruginine.

  DOI：

  10.1021/jo9515081

文献信息

• Enantiospecific Synthesis of (+)- and (−)-Ferruginine from <scp>l</scp>-Glutamic Acid. Synthesis of Tropanes <i>via</i> Intramolecular Iminium Ion Cyclization
  作者：Andrés S. Hernández、Adrian Thaler、Josep Castells、Henry Rapoport

  DOI：10.1021/jo9515081

  日期：1996.1.1

  Iminium ions, generated by decarbonylation of N-benzyl-5-[1-(methoxycarbonyl)-4-oxopentyl]-prolines, prolines, undergo intramolecular cyclization to afford 2,4-disubstituted tropanes in good yields. This transformation is also shown to be a stereospecific reaction. The value of these substituted tropanes has been demonstrated by functional group manipulation, leading to the enantiospecific synthesis of (+)-ferruginine, an alkaloid isolated from Darlinga ferruginea, and its unnatural enantiomer, (-)-ferruginine.